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Flights from Toronto to Chicago
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Flights from Toronto to Chicago Starting at NZD 167

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Sun, Feb 9|Toronto - Chicago|Porter Airlines
        NZD 204NZD 465
        56% OFF
        56% OFF
        NZD 465NZD 204

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sun, Feb 9, arriving at Midway International Airport. One-way Prices start from NZD 204 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Wed, Feb 5|Toronto - Chicago|Porter Airlines
        NZD 204NZD 465
        56% OFF
        56% OFF
        NZD 465NZD 204

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Wed, Feb 5, arriving at Midway International Airport. One-way Prices start from NZD 204 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Mon, Feb 3|Toronto - Chicago|Porter Airlines
        NZD 206NZD 465
        56% OFF
        56% OFF
        NZD 465NZD 206

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Mon, Feb 3, arriving at Midway International Airport. One-way Prices start from NZD 206 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Sat, Feb 1|Toronto - Chicago|Porter Airlines
        NZD 210
        NZD 210

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sat, Feb 1, arriving at Midway International Airport. One-way Prices start from NZD 210 including taxes and charges.

      • YYZ18:20
        2h
        Nonstop
        ORD19:20
        Mon, Feb 10|Toronto - Chicago|American Airlines
        NZD 211
        NZD 211

        Choose American Airlines flights from Toronto to Chicago. The one-way direct flight with American Airlines departs from Toronto Pearson International Airport on Mon, Feb 10, arriving at O'Hare International Airport. One-way Prices start from NZD 211 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Fri, Feb 7|Toronto - Chicago|Porter Airlines
        NZD 212
        NZD 212

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Fri, Feb 7, arriving at Midway International Airport. One-way Prices start from NZD 212 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Sat, Feb 8|Toronto - Chicago|Porter Airlines
        NZD 212
        NZD 212

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sat, Feb 8, arriving at Midway International Airport. One-way Prices start from NZD 212 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Sun, Feb 23|Toronto - Chicago|Porter Airlines
        NZD 212
        NZD 212

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sun, Feb 23, arriving at Midway International Airport. One-way Prices start from NZD 212 including taxes and charges.

      • YTZ09:30
        1h 50m
        Nonstop
        MDW10:20
        Sun, Mar 2|Toronto - Chicago|Porter Airlines
        NZD 213
        NZD 213

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Sun, Mar 2, arriving at Midway International Airport. One-way Prices start from NZD 213 including taxes and charges.

      • YTZ11:20
        1h 50m
        Nonstop
        MDW12:10
        Fri, Jan 31|Toronto - Chicago|Porter Airlines
        NZD 213
        NZD 213

        Choose Porter Airlines flights from Toronto to Chicago. The one-way direct flight with Porter Airlines departs from Billy Bishop Toronto City Airport on Fri, Jan 31, arriving at Midway International Airport. One-way Prices start from NZD 213 including taxes and charges.

      • YTO01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sun, Jan 26|Toronto - Chicago|Porter Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Toronto to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Toronto to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Porter Airlines logoPorter AirlinesAir Canada logoAir CanadaUnited Airlines logoUnited AirlinesAmerican Airlines logoAmerican Airlines

Alternative Routes from Toronto to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Toronto to Chicago.

  • Cheapest
    WestJet
    YKF
    06:30
    10h 26m
    1 transfer
    ORD
    15:56
    Region Of Waterloo International Airport - O'Hare International Airport
    Mon, Feb 24WestJet
    NZD 167
  • American Airlines
    YYZ
    18:20
    2h 0m
    Nonstop
    ORD
    19:20
    Toronto Pearson International Airport - O'Hare International Airport
    Mon, Feb 10American Airlines
    NZD 211
  • Porter Airlines
    YTZ
    11:20
    1h 50m
    Nonstop
    MDW
    12:10
    Billy Bishop Toronto City Airport - Midway International Airport
    Sat, Jan 25Porter Airlines
    NZD 344
  • Porter Airlines
    YTZ
    11:20
    1h 50m
    Nonstop
    MDW
    12:10
    Billy Bishop Toronto City Airport - Midway International Airport
    Sat, Jan 25Porter Airlines
    NZD 344
    Find More Flights

FAQ

  • When are flight tickets from Toronto (YTO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Toronto to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Toronto (YTO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 507.

  • How long does it take to fly from Toronto (YTO) to Chicago (CHI) and what is the distance?

    It takes around 1 hour 59 minutes to fly from Toronto (YTO) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Toronto (YTO) to Chicago (CHI)?

    Airlines with flights from Toronto (YTO) to Chicago (CHI): Alaska Airlines, American Airlines, United Airlines, Qantas Airways, Air Canada and Qatar Airways.

How to find a cheap flight from Toronto to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Toronto to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Toronto to Chicago

Cheapest nonstop flight priceNZD 166
Cheapest round-trip ticket priceNZD 348
Off-season for travelNovember
Peak season for travelOctober
Flight distance701.97 km
Average flight time1 hour 59 minutes
Popular airlineAmerican Airlines

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